(6S)-2,4-Di-tert-butyl-6-[(4S,5R)-3-iso-propyl-4-methyl-5-phenyloxazolidin-2-yl]phenol.

The title oxazolidine compound, C(27)H(39)NO(2), was synthesized from N-isopropyl-norephedrine. The dihedral angle between the aromatic rings is 70.33 (5)°. The N atom of the heterocycle is oriented to allow intra-molecular O-H⋯N hydrogen bonding with the hydr-oxy substituent.

Related literature

For related structures and background to chiral oxazolidines, see: Agami & Couty (2004 ▶); Anderson et al. (2010 ▶); Bourne et al. (1997 ▶); Duffy et al. (2004 ▶); Hitchcock et al. (2004 ▶); Koyanagi et al. (2010 ▶); Parrott & Hitchcock (2007 ▶); Parrott et al. (2008 ▶). The synthesis and absolute configuration assignment of the title compound is described by Parrott et al. (2008 ▶). The absolute configuration assignment is based on both optical activity measurements and on the known stereochemistry of the commercially obtained optically pure norephedrine from which it was prepared (Parrott et al., 2008 ▶). For geometry checks using Mogul, see: Bruno et al. (2004 ▶). For ring puckering analysis, see: Boeyens (1978 ▶); Cremer & Pople (1975 ▶); Spek (2009 ▶). For a description of the Jmol toolkit for the preparation of enhanced figures, see: McMahon & Hanson (2008).

Experimental

Crystal data

C27H39NO2

M = 409.59

Monoclinic,

a = 18.9564 (19) Å

b = 6.9943 (7) Å

c = 18.3388 (19) Å

β = 91.833 (2)°

V = 2430.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 140 K

0.55 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.809, T max = 0.992

14330 measured reflections

3938 independent reflections

3568 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.06

3938 reflections

275 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (McMahon & Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009074/sj2720sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009074/sj2720Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 2

C27H39NO2	F(000) = 896
Mr = 409.59	Dx = 1.119 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 4163 reflections
a = 18.9564 (19) Å	θ = 2.4–30.0°
b = 6.9943 (7) Å	µ = 0.07 mm−1
c = 18.3388 (19) Å	T = 140 K
β = 91.833 (2)°	Prism, colourless
V = 2430.2 (4) Å3	0.55 × 0.27 × 0.11 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3938 independent reflections
Radiation source: sealed tube	3568 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 30.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −26→26
Tmin = 0.809, Tmax = 0.992	k = −9→9
14330 measured reflections	l = −25→26

Refinement on F2	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.4486P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.31 e Å−3
3938 reflections	Δρmin = −0.21 e Å−3
275 parameters

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.21602 (6)	0.71916 (17)	0.60579 (5)	0.0173 (2)
C2	0.23499 (7)	0.5793 (2)	0.66002 (8)	0.0151 (3)
H2	0.2784	0.5104	0.6451	0.018*
N3	0.17413 (6)	0.4434 (2)	0.65832 (7)	0.0156 (2)
C4	0.13878 (8)	0.4652 (3)	0.58521 (8)	0.0184 (3)
H4	0.1378	0.3396	0.5591	0.022*
C5	0.18794 (8)	0.6063 (2)	0.54634 (8)	0.0168 (3)
H5	0.2272	0.5331	0.5242	0.02*
C6	0.15197 (8)	0.7273 (3)	0.48843 (8)	0.0190 (3)
C7	0.13772 (9)	0.6460 (3)	0.41968 (9)	0.0247 (4)
H7	0.1551	0.5222	0.4087	0.03*
C8	0.09812 (10)	0.7473 (3)	0.36750 (9)	0.0310 (4)
H8	0.0879	0.6913	0.3211	0.037*
C9	0.07341 (9)	0.9289 (3)	0.38248 (10)	0.0309 (4)
H9	0.0457	0.9962	0.3469	0.037*
C10	0.08921 (9)	1.0122 (3)	0.44958 (10)	0.0296 (4)
H10	0.0734	1.1381	0.4596	0.036*
C11	0.12842 (9)	0.9110 (3)	0.50231 (9)	0.0241 (3)
H11	0.1391	0.9684	0.5483	0.029*
C12	0.06366 (8)	0.5394 (3)	0.59313 (10)	0.0265 (4)
H12A	0.0356	0.4433	0.6181	0.04*
H12B	0.0424	0.5647	0.5447	0.04*
H12C	0.0648	0.6579	0.6217	0.04*
C13	0.19230 (8)	0.2421 (2)	0.67659 (9)	0.0184 (3)
H13	0.2183	0.1852	0.6353	0.022*
C14	0.23865 (9)	0.2287 (3)	0.74597 (9)	0.0239 (3)
H14A	0.2823	0.3008	0.7395	0.036*
H14B	0.2501	0.0944	0.756	0.036*
H14C	0.2133	0.2823	0.787	0.036*
C15	0.12439 (8)	0.1293 (2)	0.68651 (9)	0.0215 (3)
H15A	0.0946	0.1382	0.642	0.032*
H15B	0.099	0.1822	0.7276	0.032*
H15C	0.136	−0.0051	0.6963	0.032*
C16	0.24901 (8)	0.6727 (2)	0.73341 (8)	0.0146 (3)
C17	0.19570 (8)	0.6985 (2)	0.78395 (8)	0.0153 (3)
C18	0.21200 (7)	0.7788 (2)	0.85336 (8)	0.0157 (3)
C19	0.28182 (8)	0.8304 (2)	0.86816 (8)	0.0164 (3)
H19	0.2933	0.8853	0.9144	0.02*
C20	0.33651 (7)	0.8063 (2)	0.81889 (8)	0.0152 (3)
C21	0.31826 (7)	0.7257 (2)	0.75174 (8)	0.0154 (3)
H21	0.3539	0.706	0.7173	0.018*
O22	0.12784 (5)	0.64508 (18)	0.76713 (6)	0.0186 (2)
C23	0.15478 (8)	0.8022 (2)	0.91039 (8)	0.0177 (3)
C24	0.09529 (8)	0.9342 (3)	0.88101 (9)	0.0240 (3)
H24A	0.0751	0.8813	0.8355	0.036*
H24B	0.1145	1.0616	0.8717	0.036*
H24C	0.0585	0.9437	0.9171	0.036*
C25	0.12440 (9)	0.6043 (3)	0.92950 (9)	0.0220 (3)
H25A	0.1051	0.5433	0.8851	0.033*
H25B	0.0868	0.6198	0.9645	0.033*
H25C	0.162	0.5241	0.9511	0.033*
C26	0.18409 (9)	0.8921 (3)	0.98124 (9)	0.0224 (3)
H26A	0.1461	0.9042	1.016	0.034*
H26B	0.2033	1.019	0.9708	0.034*
H26C	0.2216	0.8107	1.0022	0.034*
C27	0.41164 (8)	0.8692 (2)	0.84125 (8)	0.0175 (3)
C28	0.41262 (9)	1.0865 (3)	0.85531 (9)	0.0217 (3)
H28A	0.3789	1.1178	0.8929	0.033*
H28B	0.3995	1.1542	0.8101	0.033*
H28C	0.4601	1.1257	0.8719	0.033*
C29	0.46469 (8)	0.8238 (3)	0.78232 (9)	0.0241 (3)
H29A	0.5118	0.8663	0.7987	0.036*
H29B	0.4508	0.8905	0.7371	0.036*
H29C	0.4654	0.6857	0.7735	0.036*
C30	0.43590 (8)	0.7636 (3)	0.91139 (9)	0.0225 (3)
H30A	0.4029	0.7905	0.9502	0.034*
H30B	0.4832	0.8074	0.9266	0.034*
H30C	0.437	0.6257	0.9021	0.034*
H22	0.1327 (12)	0.561 (4)	0.7296 (12)	0.034 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0198 (5)	0.0170 (5)	0.0150 (5)	−0.0012 (4)	−0.0024 (4)	0.0005 (4)
C2	0.0140 (6)	0.0142 (7)	0.0170 (7)	−0.0007 (5)	−0.0014 (5)	−0.0003 (5)
N3	0.0157 (5)	0.0134 (6)	0.0175 (6)	−0.0004 (5)	−0.0026 (4)	0.0003 (5)
C4	0.0189 (7)	0.0196 (7)	0.0166 (7)	−0.0020 (6)	−0.0020 (5)	0.0000 (6)
C5	0.0178 (6)	0.0184 (7)	0.0143 (6)	−0.0009 (6)	−0.0006 (5)	−0.0022 (6)
C6	0.0172 (7)	0.0242 (8)	0.0157 (7)	−0.0047 (6)	0.0015 (5)	0.0016 (6)
C7	0.0264 (8)	0.0308 (9)	0.0172 (7)	−0.0099 (7)	0.0023 (6)	−0.0016 (7)
C8	0.0317 (9)	0.0466 (12)	0.0146 (7)	−0.0189 (9)	−0.0030 (6)	0.0049 (8)
C9	0.0228 (8)	0.0445 (12)	0.0249 (8)	−0.0102 (8)	−0.0044 (6)	0.0169 (8)
C10	0.0266 (8)	0.0332 (10)	0.0292 (9)	0.0026 (7)	0.0007 (7)	0.0102 (8)
C11	0.0258 (8)	0.0278 (9)	0.0185 (7)	0.0030 (7)	−0.0011 (6)	0.0021 (7)
C12	0.0162 (7)	0.0381 (10)	0.0249 (8)	−0.0015 (7)	−0.0024 (6)	0.0101 (8)
C13	0.0178 (7)	0.0148 (7)	0.0229 (7)	0.0015 (6)	0.0016 (5)	−0.0002 (6)
C14	0.0238 (8)	0.0186 (8)	0.0290 (8)	0.0014 (6)	−0.0048 (6)	0.0047 (7)
C15	0.0231 (7)	0.0167 (8)	0.0247 (8)	−0.0019 (6)	0.0026 (6)	0.0002 (6)
C16	0.0165 (7)	0.0122 (7)	0.0150 (6)	0.0010 (5)	−0.0006 (5)	0.0000 (5)
C17	0.0136 (6)	0.0138 (7)	0.0184 (7)	0.0010 (5)	−0.0006 (5)	0.0007 (5)
C18	0.0161 (6)	0.0138 (7)	0.0171 (7)	0.0018 (5)	0.0012 (5)	0.0012 (5)
C19	0.0171 (7)	0.0176 (7)	0.0145 (6)	0.0004 (5)	−0.0007 (5)	−0.0010 (6)
C20	0.0134 (6)	0.0149 (7)	0.0172 (7)	0.0003 (5)	−0.0005 (5)	0.0010 (6)
C21	0.0143 (6)	0.0153 (7)	0.0167 (6)	0.0014 (5)	0.0020 (5)	−0.0001 (6)
O22	0.0135 (5)	0.0222 (6)	0.0201 (5)	−0.0010 (4)	0.0000 (4)	−0.0036 (5)
C23	0.0146 (6)	0.0202 (8)	0.0183 (7)	0.0013 (6)	0.0023 (5)	−0.0004 (6)
C24	0.0206 (7)	0.0260 (9)	0.0256 (8)	0.0067 (7)	0.0036 (6)	0.0019 (7)
C25	0.0213 (7)	0.0246 (9)	0.0204 (7)	−0.0038 (6)	0.0029 (6)	0.0021 (6)
C26	0.0219 (7)	0.0259 (9)	0.0197 (7)	−0.0018 (7)	0.0041 (6)	−0.0045 (6)
C27	0.0135 (6)	0.0207 (8)	0.0181 (7)	−0.0012 (6)	−0.0004 (5)	−0.0014 (6)
C28	0.0200 (7)	0.0207 (8)	0.0243 (8)	−0.0034 (6)	−0.0002 (6)	−0.0030 (6)
C29	0.0141 (7)	0.0334 (9)	0.0248 (8)	−0.0021 (6)	0.0025 (6)	−0.0082 (7)
C30	0.0170 (7)	0.0271 (9)	0.0230 (7)	0.0024 (6)	−0.0030 (6)	0.0009 (7)

O1—C2	1.4324 (18)	C16—C17	1.405 (2)
O1—C5	1.4345 (18)	C17—O22	1.3652 (17)
C2—N3	1.4947 (19)	C17—C18	1.416 (2)
C2—C16	1.512 (2)	C18—C19	1.390 (2)
C2—H2	1	C18—C23	1.539 (2)
N3—C13	1.485 (2)	C19—C20	1.407 (2)
N3—C4	1.4875 (19)	C19—H19	0.95
C4—C12	1.527 (2)	C20—C21	1.388 (2)
C4—C5	1.547 (2)	C20—C27	1.534 (2)
C4—H4	1	C21—H21	0.95
C5—C6	1.504 (2)	O22—H22	0.91 (3)
C5—H5	1	C23—C26	1.532 (2)
C6—C11	1.386 (3)	C23—C24	1.541 (2)
C6—C7	1.401 (2)	C23—C25	1.544 (2)
C7—C8	1.391 (3)	C24—H24A	0.98
C7—H7	0.95	C24—H24B	0.98
C8—C9	1.384 (3)	C24—H24C	0.98
C8—H8	0.95	C25—H25A	0.98
C9—C10	1.386 (3)	C25—H25B	0.98
C9—H9	0.95	C25—H25C	0.98
C10—C11	1.394 (2)	C26—H26A	0.98
C10—H10	0.95	C26—H26B	0.98
C11—H11	0.95	C26—H26C	0.98
C12—H12A	0.98	C27—C29	1.533 (2)
C12—H12B	0.98	C27—C30	1.541 (2)
C12—H12C	0.98	C27—C28	1.541 (2)
C13—C14	1.526 (2)	C28—H28A	0.98
C13—C15	1.526 (2)	C28—H28B	0.98
C13—H13	1	C28—H28C	0.98
C14—H14A	0.98	C29—H29A	0.98
C14—H14B	0.98	C29—H29B	0.98
C14—H14C	0.98	C29—H29C	0.98
C15—H15A	0.98	C30—H30A	0.98
C15—H15B	0.98	C30—H30B	0.98
C15—H15C	0.98	C30—H30C	0.98
C16—C21	1.395 (2)
C2—O1—C5	103.35 (11)	C17—C16—C2	122.22 (13)
O1—C2—N3	104.08 (11)	O22—C17—C16	120.56 (13)
O1—C2—C16	110.87 (12)	O22—C17—C18	119.24 (13)
N3—C2—C16	114.02 (12)	C16—C17—C18	120.20 (13)
O1—C2—H2	109.2	C19—C18—C17	117.22 (13)
N3—C2—H2	109.2	C19—C18—C23	121.78 (13)
C16—C2—H2	109.2	C17—C18—C23	120.97 (13)
C13—N3—C4	113.28 (13)	C18—C19—C20	124.06 (14)
C13—N3—C2	115.16 (12)	C18—C19—H19	118
C4—N3—C2	106.19 (11)	C20—C19—H19	118
N3—C4—C12	110.11 (12)	C21—C20—C19	116.77 (13)
N3—C4—C5	102.71 (11)	C21—C20—C27	123.82 (13)
C12—C4—C5	113.85 (14)	C19—C20—C27	119.41 (13)
N3—C4—H4	110	C20—C21—C16	121.85 (13)
C12—C4—H4	110	C20—C21—H21	119.1
C5—C4—H4	110	C16—C21—H21	119.1
O1—C5—C6	112.09 (13)	C17—O22—H22	103.2 (14)
O1—C5—C4	102.43 (11)	C26—C23—C18	112.07 (12)
C6—C5—C4	114.71 (12)	C26—C23—C24	106.97 (14)
O1—C5—H5	109.1	C18—C23—C24	110.48 (12)
C6—C5—H5	109.1	C26—C23—C25	107.66 (13)
C4—C5—H5	109.1	C18—C23—C25	109.56 (13)
C11—C6—C7	119.14 (16)	C24—C23—C25	110.02 (13)
C11—C6—C5	122.20 (14)	C23—C24—H24A	109.5
C7—C6—C5	118.51 (16)	C23—C24—H24B	109.5
C8—C7—C6	119.79 (18)	H24A—C24—H24B	109.5
C8—C7—H7	120.1	C23—C24—H24C	109.5
C6—C7—H7	120.1	H24A—C24—H24C	109.5
C9—C8—C7	120.60 (17)	H24B—C24—H24C	109.5
C9—C8—H8	119.7	C23—C25—H25A	109.5
C7—C8—H8	119.7	C23—C25—H25B	109.5
C8—C9—C10	119.83 (17)	H25A—C25—H25B	109.5
C8—C9—H9	120.1	C23—C25—H25C	109.5
C10—C9—H9	120.1	H25A—C25—H25C	109.5
C9—C10—C11	119.83 (19)	H25B—C25—H25C	109.5
C9—C10—H10	120.1	C23—C26—H26A	109.5
C11—C10—H10	120.1	C23—C26—H26B	109.5
C6—C11—C10	120.75 (17)	H26A—C26—H26B	109.5
C6—C11—H11	119.6	C23—C26—H26C	109.5
C10—C11—H11	119.6	H26A—C26—H26C	109.5
C4—C12—H12A	109.5	H26B—C26—H26C	109.5
C4—C12—H12B	109.5	C29—C27—C20	112.13 (13)
H12A—C12—H12B	109.5	C29—C27—C30	107.72 (13)
C4—C12—H12C	109.5	C20—C27—C30	109.61 (13)
H12A—C12—H12C	109.5	C29—C27—C28	108.51 (14)
H12B—C12—H12C	109.5	C20—C27—C28	109.48 (13)
N3—C13—C14	111.70 (13)	C30—C27—C28	109.35 (14)
N3—C13—C15	109.08 (13)	C27—C28—H28A	109.5
C14—C13—C15	109.52 (13)	C27—C28—H28B	109.5
N3—C13—H13	108.8	H28A—C28—H28B	109.5
C14—C13—H13	108.8	C27—C28—H28C	109.5
C15—C13—H13	108.8	H28A—C28—H28C	109.5
C13—C14—H14A	109.5	H28B—C28—H28C	109.5
C13—C14—H14B	109.5	C27—C29—H29A	109.5
H14A—C14—H14B	109.5	C27—C29—H29B	109.5
C13—C14—H14C	109.5	H29A—C29—H29B	109.5
H14A—C14—H14C	109.5	C27—C29—H29C	109.5
H14B—C14—H14C	109.5	H29A—C29—H29C	109.5
C13—C15—H15A	109.5	H29B—C29—H29C	109.5
C13—C15—H15B	109.5	C27—C30—H30A	109.5
H15A—C15—H15B	109.5	C27—C30—H30B	109.5
C13—C15—H15C	109.5	H30A—C30—H30B	109.5
H15A—C15—H15C	109.5	C27—C30—H30C	109.5
H15B—C15—H15C	109.5	H30A—C30—H30C	109.5
C21—C16—C17	119.90 (13)	H30B—C30—H30C	109.5
C21—C16—C2	117.82 (13)
C5—O1—C2—N3	−43.06 (13)	O1—C2—C16—C21	−92.31 (16)
C5—O1—C2—C16	−166.07 (12)	N3—C2—C16—C21	150.63 (13)
O1—C2—N3—C13	148.89 (12)	O1—C2—C16—C17	90.78 (16)
C16—C2—N3—C13	−90.19 (16)	N3—C2—C16—C17	−26.3 (2)
O1—C2—N3—C4	22.67 (15)	C21—C16—C17—O22	−179.16 (14)
C16—C2—N3—C4	143.59 (13)	C2—C16—C17—O22	−2.3 (2)
C13—N3—C4—C12	115.78 (16)	C21—C16—C17—C18	0.2 (2)
C2—N3—C4—C12	−116.86 (14)	C2—C16—C17—C18	177.09 (14)
C13—N3—C4—C5	−122.62 (14)	O22—C17—C18—C19	179.78 (14)
C2—N3—C4—C5	4.73 (15)	C16—C17—C18—C19	0.4 (2)
C2—O1—C5—C6	169.17 (12)	O22—C17—C18—C23	1.4 (2)
C2—O1—C5—C4	45.70 (14)	C16—C17—C18—C23	−178.02 (14)
N3—C4—C5—O1	−30.41 (15)	C17—C18—C19—C20	−0.5 (2)
C12—C4—C5—O1	88.60 (15)	C23—C18—C19—C20	177.89 (15)
N3—C4—C5—C6	−152.11 (13)	C18—C19—C20—C21	0.0 (2)
C12—C4—C5—C6	−33.09 (19)	C18—C19—C20—C27	179.87 (15)
O1—C5—C6—C11	−20.2 (2)	C19—C20—C21—C16	0.7 (2)
C4—C5—C6—C11	96.10 (18)	C27—C20—C21—C16	−179.21 (15)
O1—C5—C6—C7	164.23 (13)	C17—C16—C21—C20	−0.8 (2)
C4—C5—C6—C7	−79.51 (18)	C2—C16—C21—C20	−177.78 (14)
C11—C6—C7—C8	−2.4 (2)	C19—C18—C23—C26	1.8 (2)
C5—C6—C7—C8	173.36 (14)	C17—C18—C23—C26	−179.90 (15)
C6—C7—C8—C9	0.9 (2)	C19—C18—C23—C24	120.96 (16)
C7—C8—C9—C10	1.1 (3)	C17—C18—C23—C24	−60.72 (19)
C8—C9—C10—C11	−1.6 (3)	C19—C18—C23—C25	−117.67 (16)
C7—C6—C11—C10	1.9 (2)	C17—C18—C23—C25	60.66 (18)
C5—C6—C11—C10	−173.66 (16)	C21—C20—C27—C29	−2.7 (2)
C9—C10—C11—C6	0.1 (3)	C19—C20—C27—C29	177.39 (15)
C4—N3—C13—C14	170.85 (12)	C21—C20—C27—C30	−122.31 (16)
C2—N3—C13—C14	48.35 (18)	C19—C20—C27—C30	57.81 (19)
C4—N3—C13—C15	−67.93 (16)	C21—C20—C27—C28	117.75 (17)
C2—N3—C13—C15	169.56 (12)	C19—C20—C27—C28	−62.13 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···N3	0.91 (3)	1.75 (2)	2.6180 (17)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O22—H22⋯N3	0.91 (3)	1.75 (2)	2.6180 (17)	158 (2)